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Will Eno, at home in Brooklyn, N.Y., says he’s been fascinated with the big, looming questions for as long as he can remember — going back to his days as a quiet kid growing up in the suburbs northwest of Boston.

NEW YORK — A preoccupation with cosmic quandaries — and with the pain and loneliness that often mark human existence — pervades the plays of Will Eno, from his 2005 Pulitzer Prize finalist “Thom Pain (based on nothing)” to his most recent dramas, “The Realistic Joneses” and “Title and Deed.” In his 2010 play “Middletown,” which begins performances Wednesday at the Cambridge YMCA Theatre, produced by Actors’ Shakespeare Project, the characters’ conversations are laced with wry, mordant musings on life and death in the face of a vast and unknowable universe.

Over a cup of tea in the kitchen of his apartment in Greenpoint, Brooklyn, Eno, 47, says that he’s been fascinated with the big, looming questions for as long as he can remember — going back to his days as a quiet kid growing up in the suburbs northwest of Boston.

“It may be the most pretentious thing in the world to another person, but it feels very native and unpretentious to me, or I think of these things in fairly unpretentious terms,” says Eno. “Maybe metaphysics is for people who can’t solve their own emotional troubles. But I actually feel better than I’ve ever felt in my life these days, and yet I am still fascinated by those questions.”

Eno’s “Middletown” could be considered a meditation on birth and death and the lives burning bright in between.

“We spend a lot of time thinking about the end and the beginning, in kind of self-aggrandizing ways. We talk about the miracle of birth and the mystery of death. But, by definition, all of our lives take place in the middle of those two sort of unknowable events, in this great and often unexamined middle,” Eno says. “So I wanted to write a play that put some thoughts and feelings in the air about the miracle and the mystery and that alluded to deep and unknown forces. But then really just have people going to the store and fixing the sink and going through the normal things of looking for love and getting up in the morning. Because that’s how we live.”

While Eno counts Samuel Beckett and Don DeLillo as influences and Edward Albee as a mentor, he also acknowledges that “Middletown,” which in 2010 captured the inaugural Horton Foote Prize for Promising New American Play, owes something of an inspirational debt to Thornton Wilder’s “Our Town.”

“That play had a great effect on me, but I never felt it needed an ‘update’ or a ‘newer version.’ So, if anything, I made conscious efforts to make sure ‘Middletown’ went a separate way,” he says. “I think ‘Middletown’ tries to look at the accumulation and effect of the tiny moments that make up our lives — and how we are constantly vulnerable to these tiny moments, which may in fact change the angle of our entire life, or not.”

“Middletown,” which premiered off-Broadway at the Vineyard Theatre two seasons ago, unfolds as a series of fleeting, tenuous, and sometimes strained interactions between various townspeople. Amidst the cookie-cutter homes, a tentative friendship is developing between newcomer Mrs. Swanson, a young woman who’s about to start a family with her oft-absent husband, and the lonely, anxious John Dodge, an itinerant handyman who confesses to being between jobs.

Eno’s hamlet is populated with archetypal figures. But each one is a little skewed — a stolid, prickly Cop; a brooding, troubled Mechanic; a cheerful, dry-witted Librarian; and a compassionate yet candid Female Doctor. Like the Stage Manager in “Our Town,” Eno’s characters often speak directly to the audience. But the people in “Middletown” have a strange knack for articulating the secret fears and niggling anxieties, the hidden hopes and dashed dreams beneath the genial pleasantries of small-town life.

“I get these awful panic attacks,” confesses John Dodge. “They’re actually how I stay in shape.”

“The characters voice awkward, difficult things that many of us think but don’t necessarily say out loud. So it strikes this uncomfortable but funny chord,” says Doug Lockwood, the Actors’ Shakespeare Project founding member who’s directing “Middletown.” “In rehearsal, all the actors keep talking about how there’s no lying in this play. It’s a grave honesty that society doesn’t usually welcome.”

The challenge for actors, says Lockwood, is to speak those lines in a simple, unadorned way and to balance letting the play breathe with keeping it in forward motion. “The tempo is really important,” he says. “If we aren’t careful, it can slip into a kind of ponderousness that could be deadly.”

Eno, who grew up in Billerica, Car­lisle, and Westford, went to Concord-Carlisle High School and was a competitive cyclist from the age of about 13 until his early 20s. He made the junior national team and spent time at the Olympic training center in Colorado Springs, had several top-10 finishes, and earned a silver medal in the national championships. Because of his intense focus on cycling, Eno says, he’d never really figured out who he was and what he wanted to do with his life. He attended the University of Massachusetts Amherst for three years, but dropped out and moved to New York.

“There was at least a good decade or so when I couldn’t find any meaning or meaningful structure to my life other than that I had to go to paint some house somewhere or proofread a textbook manuscript,” he says.

He gravitated toward the idea of becoming a writer, but didn’t gain the necessary focus and energy until he encountered Gordon Lish, the literary editor. Eno says that Lish “woke me up to the seriousness of the whole thing — both writing and life itself” and has become his most important mentor and a close friend.

“He said, ‘There’s this stuff, like death, that we all face, and you can gripe about that or call that a reason to not do anything, or you can get down to work,’ ” he recalls. “I suppose a lot of people don’t like or respond to how he teaches. But I think since I came from a sports background rather than an encouraging liberal arts tradition, his demanding approach actually made sense to me. If you were going to try to run faster, and I was coaching you, you wouldn’t resent me if I said, ‘No, run another lap.’ ”

Eno, whom New York Times critic Charles Isherwood once famously described as “a Samuel Beckett for the Jon Stewart generation,” can sometimes sound like the anxious, reflective characters in his plays, with a similar easygoing bonhomie and a surreal, offbeat sense of humor. He says that he’s not exactly sure how his singular writing style came about. But he does allow that “speech was not a big thing around the house, growing up. So I developed a kind of anxiety about talking. It was kind of beyond shyness.”

“For a lot of years, a lot of what happened, happened inside my head. And I guess it’s possible, maybe even easier, to develop a style when it’s all just words ricocheting and echoing around in your head.”

When he was young, he also suffered from what he calls “big and ridiculous and probably very common struggles with identity — with even just the simplest thing of trying to say my name to people. … I had a problem with just being, and I always had a lot of trouble sorting out my feelings or finding someone to tell them to. And so I thought the world was sad.”

These days, Eno says, he’s in a great place in life and believes in love “in a very calm and real way that is different from ways I’ve felt before.”

“There’s a bunch of people in my life that I really trust and who make me feel trustworthy, and that’s something I’ve not really known too much in my life before,” he says.

Still, his fascination with life and death and the nature of existence remains unabated. But that doesn’t mean he’s a depressed or dour soul. In fact, thinking about death, he suggests, helps us all to better understand and affirm life.

“It’s hard to be a human being. It’s complicated — and complicated in ways we’ll probably never fully be able to see,” he says. “I wrote this play and mean it to be a kind of testament to the difficulty of consciousness, or a picture of the complications of the simplest life.”